Cheap Flights from San Jose to Chicago

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Flight deals from San Jose to Chicago

Looking for a cheap last-minute deal or the best return flight from San Jose to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from San Jose to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Jose to Chicago flights are currently cheapest in April.

Direct flights from San Jose to Chicago

Alternative San Jose to Chicago routes

Looking for the cheapest, fastest or easiest route from San Jose to Chicago? You could fly into the following airports instead.

San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight foundج.م.‏ 2,987
Cheapest month to flyApril
Average flight time4 hrs, 15 mins
Most popular airlineSouthwest Airlines
Average flights per week22

Finding cheap flights from San Jose to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from San Jose to Chicago is ج.م.‏ 7,624. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 15 minutes is the average flight time from San Jose to Chicago.
Southwest Airlines and United fly direct from San Jose to Chicago.
As of March 2025, there are 22 flights per week flying from San Jose to Chicago.
The cheapest month to fly from San Jose to Chicago is usually March 2025.
If you're flying from San Jose, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from ج.م.‏ 7,624.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Jose to Chicago on Wednesday, 7 May 2025.
Yes – the average flight time is 4 hours and 15 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Spirit Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is United.

Travelling from San Jose to Chicago: what you need to know

  • San Jose's main airport is Norman Y. Mineta San Jose International Airport (SJC). Explore your departure options from this base when searching for flights from San Jose to Chicago.

  • When it comes to touching down in Chicago, O'Hare International Airport (ORD) is a key hub. Another is Chicago Midway International Airport (MDW).

  • 4 hours 10 minutes is the average journey time for a direct flight from San Jose to Chicago. Based in the UTC-5 timezone, Chicago is 2 hours ahead of San Jose.

  • The busiest route for flights from San Jose to Chicago is from Norman Y. Mineta San Jose International Airport (SJC) to O'Hare International Airport (ORD). You can select from 10 services every week between these two airports. If you want to get going first thing, the earliest flight from SJC to ORD is the 06:21 United Airlines option. If you prefer to travel later, the last departure is at 23:00 with United Airlines.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to board your flight from San Jose to Chicago.

  • Heading away during a peak time like a bank holiday? Expect longer queues at security and check-in. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • You don't need your passport or a visa to travel within United States. You will need a valid proof of identity though, like a driver's licence or ID card. Put them on your packing list once you've booked your cheap flights from San Jose to Chicago.

Flying from San Jose

Norman Y. Mineta San Jose International Airport (SJC)

  • You can get a direct flight from San Jose to Chicago departing from Norman Y. Mineta San Jose International Airport (SJC). Start your journey at SJC and arrive at O'Hare International Airport (ORD).

  • Book your direct flight from San Jose to Chicago with United Airlines. This leading airline operates services from SJC.

  • We make it easy to find a flight from San Jose to Chicago with a stopover. To see your options departing from Norman Y. Mineta San Jose International Airport, deselect 'Direct flights only.' Next, choose a flight offering a stop long enough to tour your chosen city. Top stopovers include:

    • Nashville International Airport (BNA)

    • Los Angeles International Airport (LAX)

    • Harry Reid Airport (formerly McCarran Airport) Airport (LAS)

  • SJC is around 6 kilometres from central San Jose. If you're catching a cab, driving or ride-sharing from the centre, it'll take you 12 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the journey time to be approximately 44 minutes.

  • Catching an early flight from San Jose to Chicago? Avoid the last-minute rush to the airport (and get some extra shut-eye) by choosing one of these stays near Norman Y. Mineta San Jose International Airport:

Arriving in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

How to find the cheapest flights from San Jose to Chicago

  • The lowest price we've seen for a one-way ticket from San Jose to Chicago is ج.م.‏ 2,987. For a return flight on this route, the best price is ج.م.‏ 7,624. Depending on when you book and the availability, these fares can change.

  • To snag cheap tickets from San Jose to Chicago, book your journey 9 months ahead of your departure.

  • Organise your trip for May. That's the cheapest month for flight tickets from San Jose to Chicago. If you're flexible with your travel dates, use the 'Whole month' tool to see the lowest price across every month.

  • Create a Price Alert for cheap tickets from San Jose to Chicago. You don't need to look every day to find out if fares have dropped. We'll notify you the moment there's a change in price.

  • Use filters to tailor your flights from San Jose to Chicago. Simply enter your ideal departure and arrival times, airlines and number of stops. Or sort your results by 'Cheapest' to find the best deals.

Best time to go to Chicago

  • August is the most popular month for flights from San Jose to Chicago. To escape the crowds, head to Chicago in February.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from San Jose to Chicago in this month if this is the kind of weather you like.

  • January sees average temperatures of between -12ºC and 3ºC. Search for cheap tickets from San Jose to Chicago sometime then if you want to travel when it's cooler.

More about Chicago

  • Once you've booked your flight from San Jose to Chicago, think about where you'll stay in this city. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to discover in this city it can be hard to figure out where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are top attractions which should feature on every Chicago itinerary.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from San Jose to Chicago isn't our only cool trick. Check out our car rentals in Chicago and have more freedom to explore. We search for deals from trusted car rental companies and put them all in one place. You can instantly compare offers and then book with no fees.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.